Skyler Gast

Enthusiast
DISC Type : i

Director, Technology Strategy and Delivery Lead at X BY 2

Austin, Texas Metropolitan Area, United States

Overview

Skyler Gast is a technology strategy and delivery Director at X by 2, specializing in the healthcare sector. He leads projects involving system modernization, AI solutions, and provider data integration. He holds a Bachelor of Science from The University of Texas at Arlington and previously led a 50-person engineering organization at CPI Card Group.

Outside of his corporate role, Skyler is an entrepreneur passionate about solving everyday problems with technology. He founded SchoolChatter, an application designed to reduce school email overload for parents, and also created a youth sports coaching app called quicksub. fun, reflecting his focus on family and community-oriented software solutions.

He developed a software product for parents that successfully completed a Google security audit.

Personality Overview

Optimistic

Story Driven

Non-Confrontational

Unlike D or C types, they are convinced more by stories and testimonials.  They agree with others often, so exercise caution when relying on their word. They are more about building relationships than just cutting deals.

Topics They Care About

AI in Healthcare
Leads AI strategy at X by 2 and actively promotes the company's machine learning patient flow platform, Choreo, in his public communications.
Parenting Technology
Founded SchoolChatter, an app specifically designed to solve the problem of school email overload for parents, a personal project he has been building.
Entrepreneurial Ventures
Has a history of founding technology startups, including SchoolChatter and hi-er, which was described as a "tinder for jobs" in Australia.

Media Appearances

Skyler has no verified media appearances

Work History

1-2024
Director, Technology Strategy and Delivery Lead at X BY 2
9-2022 - 12-2023
Associate Director, Technology Strategy and Delivery Lead at X BY 2
10-2025
Founder at SchoolChatter by S2 Software
1-2021 - 8-2023
Co-Founder at hi-er
6-2021 - 8-2022
Director of Software Solutions at CPI Card Group

Education

BS from The University of Texas at Arlington

More Information

Social Presence :

Prographics :

Exp : 9 Location : Austin, Texas Metropolitan Area, United States Job Level : Mid-senior Designation : Director, Technology Strategy and Delivery Lead at X BY 2
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Insights For Selling To Skyler

During A Call Or A Meeting

DO's

  • Maintain high, positive energy and convey confidence
  • Refer to interesting customer testimonials and stress on great customer experience
  • Compliment them about their personality if you get a chance

DONT's

  • Don't be critical or challenge them openly, they can react defensively
  • Don’t be too formal with them, they trust informality more
  • Don’t ask too many questions in one go, weave them into the flow

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Skyler is

  • Relationships and rapport matter to them, but so does the value of the product.
  • Will you ever get a clear answer from Skyler

  • They probably won't say no directly.


Insights For Deal Planning

    How fast (or slow) will Skyler move?

  • They are not the ones to make fast decisions, even while they stay committed.
  • Can Skyler take some risk or not?

  • If it seems really necessary, they can take small risks.

You And Skyler

Personality Compatibility


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